sodium (2R)-1-{2-[(2R,3R,6R)-2-hydroxy-6-[(3E,5E,7E,9S,11R,13S,14R,15E,17R,19E,21R)-14-hydroxy-22-[(1S,3S,4R)-4-hydroxy-3-methoxycyclohexyl]-2,13-dimethoxy-3,9,11,15,17,21-hexamethyl-12,18-dioxodocosa-3,5,7,15,19-pentaen-1-yl]-3-methyloxan-2-yl]-2-oxoacetyl}piperidine-2-carboxylate

• ChemBase ID: 177374
• Molecular Formular: C51H78NNaO13
• Molecular Mass: 936.15369
• Monoisotopic Mass: 935.53708584
• SMILES: [C@@H]1([C@H](C[C@@H](CC1)C[C@H](/C=C/C(=O)[C@@H](/C=C(/[C@H]([C@@H](C(=O)[C@@H](C[C@@H](/C=C/C=C/C=C(/C(C[C@H]1CC[C@H]([C@@](O1)(C(=O)C(=O)N1[C@H](CCCC1)C(=O)[O-])O)C)OC)\C)C)C)OC)O)\C)C)C)OC)O.[Na+]
• Canonical SMILES: CO[C@H](C(=O)[C@@H](C[C@@H](/C=C/C=C/C=C(/C(C[C@H]1CC[C@H]([C@](O1)(O)C(=O)C(=O)N1CCCC[C@@H]1C(=O)[O-])C)OC)\C)C)C)[C@@H](/C(=C/[C@H](C(=O)/C=C/[C@@H](C[C@@H]1CC[C@H]([C@H](C1)OC)O)C)C)/C)O.[Na+]
• InChI: InChI=1S/C51H79NO13.Na/c1-31(26-35(5)45(55)47(64-10)46(56)36(6)28-34(4)41(53)23-19-32(2)27-38-21-24-42(54)44(29-38)63-9)16-12-11-13-17-33(3)43(62-8)30-39-22-20-37(7)51(61,65-39)48(57)49(58)52-25-15-14-18-40(52)50(59)60;/h11-13,16-17,19,23,28,31-32,34-35,37-40,42-44,46-47,54,56,61H,14-15,18,20-22,24-27,29-30H2,1-10H3,(H,59,60);/q;+1/p-1/b13-11+,16-12+,23-19+,33-17+,36-28+;/t31-,32+,34-,35-,37-,38+,39-,40-,42-,43?,44+,46-,47-,51-;/m1./s1
• InChIKey: DNMSBJYMPJMFNS-NKHLPUFYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2R)-1-{2-[(2R,3R,6R)-2-hydroxy-6-[(3E,5E,7E,9S,11R,13S,14R,15E,17R,19E,21R)-14-hydroxy-22-[(1S,3S,4R)-4-hydroxy-3-methoxycyclohexyl]-2,13-dimethoxy-3,9,11,15,17,21-hexamethyl-12,18-dioxodocosa-3,5,7,15,19-pentaen-1-yl]-3-methyloxan-2-yl]-2-oxoacetyl}piperidine-2-carboxylate
• IUPAC Traditional name: sodium (2R)-1-{2-[(2R,3R,6R)-2-hydroxy-6-[(3E,5E,7E,9S,11R,13S,14R,15E,17R,19E,21R)-14-hydroxy-22-[(1S,3S,4R)-4-hydroxy-3-methoxycyclohexyl]-2,13-dimethoxy-3,9,11,15,17,21-hexamethyl-12,18-dioxodocosa-3,5,7,15,19-pentaen-1-yl]-3-methyloxan-2-yl]-2-oxoacetyl}piperidine-2-carboxylate
• Synonyms: (19E/Z)-seco Rapamycin Sodium Salt, >85% By HPLC; [2R-[2α,2(S*),3α,6β[2S*,3E,5E,7E,9S*,11R*,13R*,14R*,15E,17R*,19E/Z,21R*,22(1S*,3R*,4R*)]]]-1-[Oxo[tetrahydro-2-hydroxy-6-[14-hydroxy-22-(4-hydroxy-3-methoxycyclohexyl)-2,13-dimethoxy-3,9,11,15,17,21-hexamethyl-12,18-dioxo-3,5,7,15,19-docosapentaenyl]-3-methyl-2H-pyran-2-yl]acetyl]-2-piperidinecarboxylic Acid Monosodium Salt

Database IDs

• PubChem SID: 164233284
• PubChem CID: 71751979

CALCULATED PROPERTIES

• Acid pKa: 3.7221262
• H Acceptors: 13
• H Donor: 3
• LogD (pH = 5.5): 6.159605
• LogD (pH = 7.4): 4.6394453
• Log P: 7.9370494
• Molar Refractivity: 264.6473 cm^3
• Polarizability: 97.77067 Å^3
• Polar Surface Area: 209.26 Å^2
• Rotatable Bonds: 24
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Yellow Solid
• Melting Point: 120-122°C

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - R124010

A decomposition product of Rapamycin (R124000).

REFERENCES

• Yatscoff, R.W., et all.: Ther. Drug Monit., 17, 666 (1995)
• Wacher, V.J., et al.: J. Pharm. Sci., 87, 1322 (1995)